The present invention relates to a process for preparing an optically active 3-chloro-1,2-propanediol by employing microorganism which can selectively metabolize (R)- or (S)-3-chloro-1,2-propanediol.
The optically active 3-chloro-1,2-propanediol is a useful intermediate for synthesizing a variety of drugs and optically active compounds having physiological activity. For example, (R)-3-chloro-1,2-propanediol have been used for synthesizing L-carnitine (Japanese Unexamined Patent Publication No. 165352/1982).
As the process for preparing (R)-3-chloro-1,2-propanediol, the method employing methyl-5-chloro-5-deoxy-.alpha.-L-arabinofuranoside [Hayden F. Jones, Chemistry and Industry, p 538, 15 July, 1978], the method employing 1,2,5,6-diacetonyl-D-mannitol [H. Jackson et al., Chem. -Biol. Interactions, 13, p 193 (1976): Y. Kawakami et al., Journal of Organic Chemistry, 47, p 3581 (1982)]and the like are known.
As the process for preparing (S)-3-chloro-1,2-propanediol, the method employing methyl-6-chloro-6-deoxy-.alpha.-D-glucopyranoside (DE Patent No. 2743858), the method employing 1,2,5,6-diacetonyl-D-mannitol [K. E. Porter et al., Chem. -Biol. Interactions, 41, p 95 (1982)]and the like are known.
However, the above processes are not suitable for the industrial production due to disadvantages such as difficulty in obtaining the starting material and complicated steps. Therefore, an industrially advantageous process has been earnestly desired for preparing the optically active 3-chloro-1,2-propanediol.
As a result of the continuous effort of the present inventors to establish an industrial process for preparing the optically active 3-chloro-1,2-propanediol, which hitherto has been prepared by the complicated procedures employing expensive starting materials, it was found that (R)- or (S)-3-chloro-1,2-propanediol can be easily prepared by subjecting low-priced (R,S)-3-chloro-1,2-propanediol to the action of microorganism to selectively metabolizing (S)- or (R)-3-chloro-1,2-propanediol.